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What to Do in Millerton: A 24-Hour Guide to the Sweetest Small Village

What to Do in Millerton: A 24-Hour Guide to the Sweetest Small Village

With boutique shops and bustling restaurants, the Dutchess County spot is a busy community in a small package.

BY ROBERT RUBSAM

Published: 07/03/2019

Main Street Historic District (Millerton, New York)

DOUG KERR // WIKIMEDIA COMMONS

Set into the hills of northeastern Dutchess County, Millerton is about as close as you can get to Connecticut without crossing the state border. Though small, the village sits along the soaring Taconic Range and is surrounded by rolling fields, making it an ideal hiking and biking destination.

For prospective Hudson Valley day trippers, there’s plenty to do right in town or just a short drive away. Take a look at our guide and then plan your own ideal trip to Millerton.

Oakhurst serves a healthier, more organic spin on typical diner food, spicing up the old reliables of omelets and pancakes with avocado toast, pinto bean plates, and decent doses of kale. Many ingredients are locally sourced and, while serving sizes are a little smaller than your average diner, unexpected flavors abound, making for a perfectly satisfying start to the day.

New York City-based chain Irving Farm recently moved its roasting facilities up to Millerton, and a trip to their nearby cafe for a taste is absolutely worth your time. Visit the lovely Irving Farm Coffee House, offering an inviting sit-down experience in a warm setting just a mile down the road.

Millerton is home to the headquarters of Harney & Sons, as well as the 90,000 sq. ft. factory where the leading tea brand receives, blends, and packages the dozens of fine teas it distributes around the country. For anyone who wants an insider glimpse into the behind-the-scenes happenings at the factory, the company offers a tour of the whole process, with stops at tasting, sacheting, brewing, and more.

One of the earliest in the region, this excellent rail trail heads south out of town along the Webatuck Creek, passing 10.6 miles through roads, woods, and fields before reaching the Wassaic Station. Unpaved and undeveloped sections have been purchased, with the goal of extending it for 46 miles, all the way to Chatham. It’s a pleasant walk and an easy roundtrip by bike.

See website for trailhead locations

4 p.m. – Enjoy boutique shops on Main Street

Main Street is short but packed with notable shops and boutiques, from the original Oblong Books to several antiques shops and the Harney & Sons storefront with tasting room and shop. Those looking for something a little heavier can walk up to Gordon R. Keeler’s, one of the last remaining local appliance stores, or to Country Gardeners for all their floral needs.

This independent theater shows a mix of blockbusters, prestige dramas, and scrappy indies across its multiple screens. It also displays art and hosts local authors and filmmakers for special talks. If you need to relax or want to keep quiet for an hour or two, The Moviehouse is worth a stop.

Just across the border in Lakeville, Connecticut, this sprawling complex has 40 guest rooms and suites, as well as several cottages and houses for rent on a shady lake. Open all year round, the Inn also houses a spa, yoga, restaurant, and more, making it the ideal place to spend the rest of your relaxing weekend.